First Southern Cuba expedition

The First Southern Cuba expedition (September 1719) occurred when the pirate captain Edward Kenway and his ship, the Jackdaw, engaged in pirating off the southern coast of Cuba, plundering three Spanish ships. Kenway left the island of Isla de la Juventud and decided to plunder several Spanish Navy vessels along the way, targeting the frigates Guadalupe and San Pedro y San Pablo for their large cargoes of metal. Three Spanish ships were sunk by Kenway as he sailed from Isla de la Juventud to attack the fort at Dry Tortuga.

Pirates

 * Pirates.png Jackdaw - brig

Spanish

 * Flag of Spain 2.png Guadalupe - frigate
 * Flag of Spain 2.png San Pedro y San Pablo - frigate
 * Flag of Spain 2.png Paloma Blanca - schooner